Bill Simmons Makes Case For Celtics Landing Damian Lillard In Trade

Damian Lillard reportedly wants to play for the Miami Heat now that he’s requested a trade from the Portland Trail Blazers.

That doesn’t guarantee Lillard ultimately will take his talents to South Beach, though. The seven-time All-Star doesn’t have a no-trade clause, and the Blazers reportedly intend to explore all options before dealing their longtime franchise cornerstone.

Might that process open the door for a trade to the Boston Celtics?

The Ringer’s Bill Simmons can’t shake the idea of Lillard landing with Boston, perhaps as part of a three-team blockbuster that also involves Jaylen Brown.

“I don’t see a trade, other than the Miami trade, which I don’t think is going to happen, that will propel (Lillard) to some sort of, ‘oh, now he’s on the cusp,’ unless it’s the Celtics,” Simmons said Monday on “The Bill Simmons Podcast.” “And that’s why — now, Jaylen Brown could sign this extension in five minutes and this will be moot, but I just keep circling that trade wondering, it’s starting to make more and more sense to me.”

“I think there would have to be a third team,” Simmons added. “I think Jaylen would have to go to, like, Houston. And then Houston would have to send stuff to Portland. And then Portland would send Dame to Boston. But if (Lillard) wants to win a title, and it’s not Miami, where else is it? What guarantees him to actually be close to being in the mix? You go through the teams, and everybody either has their team already or they can’t make the trade.”

What trade actually gets Dame closer to being in the mix to win a title?@BillSimmons and @ryenarussillo discuss the complications of Dame’s trade request. pic.twitter.com/Oql6XBFYwB

— The Ringer (@ringer) July 3, 2023

Brown is eligible for a supermax contract extension this offseason, raising questions about his long-term future in Boston. The Celtics are positioned for sustained success with the tandem of Brown and Jayson Tatum, but they’ve also been unable to get over the hump in search of Banner 18. Trading Brown in a deal for Lillard would completely change Boston’s DNA, especially on the heels of the C’s trading Marcus Smart in a three-team swap for Kristaps Porzingis.

Is Celtics president of basketball operations Brad Stevens ready for such a seismic shift? One could argue he should resist the urge. Brown is 26, whereas Lillard turns 33 this month, and the latter seemingly wants no part of playing in Boston.

But this is what NBA summers are all about: Dreaming up wild hypotheticals that might or might not come to fruition. And Lillard-to-Boston is an even more fascinating scenario than him ending up in Miami.

For what it’s worth, DraftKings Sportsbook as of Monday night had the Heat as -300 favorites to be Lillard’s next team. The Celtics were second on the betting board at +550, ahead of the Los Angeles Clippers (+800), the Philadelphia 76ers (+1000) and a return to the Trail Blazers (+1200).